Formal total synthesis of aspergillide A

Yuko Izuchi; Nobuhiro Kanomata; Hiroyuki Koshino; Yayoi Hongo; Tadashi Nakata; Shunya Takahashi

doi:10.1016/j.tetasy.2011.01.016

Formal total synthesis of aspergillide A

Yuko Izuchi, Nobuhiro Kanomata, Hiroyuki Koshino, Yayoi Hongo, Tadashi Nakata, Shunya Takahashi

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C₄-C₁₄ backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI₂-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.

Original language	English
Pages (from-to)	246-251
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	22
Issue number	2
DOIs	https://doi.org/10.1016/j.tetasy.2011.01.016
Publication status	Published - 2011 Jan 31

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.",

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AU - Izuchi, Yuko

AU - Kanomata, Nobuhiro

AU - Koshino, Hiroyuki

AU - Hongo, Yayoi

AU - Nakata, Tadashi

AU - Takahashi, Shunya

PY - 2011/1/31

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AB - The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.

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